Conformational analysis of the four 3-methyl-isopropylphenol isomers (thymols) by molecular orbital calculations and X-ray crystal structure determinations |
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| Authors: | G Bertholon A Thozet M Perrin C Decoret |
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| Institution: | 1. Groupe de Recherches sur les phénols. Associés au C.N.R.S.: E.R.A. 600, Université Claude Bernard Lyon I, 69622 Villeurbanne Cedex France;2. Laboratoire de Minéralogie-Christallographie. Associés au C.N.R.S.: E.R.A. 600, Université Claude Bernard Lyon I, 69622 Villeurbanne Cedex France;3. Groupe de recherches de Physique moléculaire et de Chimie organique quantique. Associés au C.N.R.S.: E.R.A. 600, Université Claude Bernard Lyon I, 69622 Villeurbanne Cedex France |
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| Abstract: | PCILO calculations have been used in a conformational investigation of 3-methyl-x-isopropylphenols (thymol isomers), including a study of the barrier to internal rotation of substituents. The results of the calculations are in good agreement with those available from experimental crystal structure determinations, except for 3-methyl-6-isopropylphenol. For the latter the calculated most stable conformer cannot form a crystal with hexamers bonded by H bonds, as is determined by crystallography. The heights of the barriers to internal rotation of the substituents are compared with the available experimental data and discussed in terms of steric hindrance. |
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